Having this urge to crossdress was always a conflict. I knew that it was wrong (I had been told) but I couldn't help my desire to do it. It was a difficult age with hormones all over the place and still a child but becoming a man.
I can remember I had a cuddly toy on my bed. It was old and falling to bits but I used it to keep a pair of knickers in. At night I could take them out and wear them in bed. Still a child but sexually aware.
All sorts of contradictions were going through my head. If I wanted to dress as a woman I must be gay. But I didn't fancy other boys. Nobody to talk to or ask. I used to say to myself if I didn't get a girl friend then I must be gay. But I was paralysed by shyness which stopped me talking to girls. All the time I'm longing to be close to a girl and little did I realise that my crossdressing was a substitute for a girl friend. I was my own girl friend!
After I left school and started working my life changed.
I made some good friends and sport and alcohol took over. But also women!
In comparison to my peers I was probably late in losing my virginity. I was 18. I desperately wanted to but it meant getting a girl friend. I still found it difficult to talk to women I fancied but my crossdressing had waned.
I lost my virginity on an 18 to 30 holiday (that ages me lol). A girl sort of attached herself to me and well, the rest is history. God it was so good.
Through my 20s I had quite a few girl friends. Some of them married! In each case they did the running. I can only remember plucking up the courage to ask one girl out and that was at a night club after being given every signal she was interested. I had enough sex to keep me happy and my crossdressing stopped altogether. Reflecting on it I still found how some girls looked erotic but I didn't wear any women's clothes.
Sex was nearly always instigated by the woman. I always considered myself respectful and would never force myself on a girl. It had to be her choice no matter how much I wanted to have sex. Maybe I should have taken the lead but I was never one of those guys who would shag anything that moved. There was more to sex than getting my rocks off.
I was 28 when I got married. My future wife moved in about a year before we married and I had access to a whole new wardrobe. I did, on a few occasions borrow her stuff but it was not regular and only ever a quick session. Mainly just lingerie. I didn't dress to the extent I had when I was younger and it was just an aid to masturbation so didn't really register. It was maybe a handful of times in 7 or 8 year.
But then it returned with a vengeance in my late 30s. I'll cover this in part 3.
Katie x
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You can see where you're similar you two but also differ slightly
Looking forward to part 3
Having this urge to crossdress was never a conflict for me from an early age right through, it was just something I liked to do.
Early on I had no comprehension it was weird I just liked the feel, later on it became sexual as I was 10 to teens I’d get off on it and hid it because I didnt want anyone to know what a little perve I was wearing lingerie and masterbating.
I didn’t know it was wrong didnt think it strange for all I knew everyone did it but it didn’t worry me at all at any age to my age today that I was doing something wrong it was only clothing it was only dressing like a woman as rational as that.
I never smuggled any items of clothing into my bedroom to wear at night. I was limited to little opportunities when home alone which was rare like it’s rare now probably to the same sort of frequency maybe once per month.
I never once thought if I wanted to dress as a woman I must be gay this never once entered my head I was straight I loved women and that was that.
When Esme asked me if I was gay it was a WTF moment no I’m not gay where did that come from.
My research on telling her wasn’t World wide web based it was from my own thoughts and experiences.. It wasn’t until after she asked that question that I looked on the internet and found it was a common question and the answer was still hell no I’m not gay I love women.
Shyness was an infliction of mine too and when dressed I’d think of girls I fancied or older women lol and id get myself off as young boys do.. So some form of substitution for a Girlfriend being so shy was maybe fantasy and being dressed myself.
After I left school, college and Uni and started working my life changed also as it comes with more responsibility and the formation of stress no matter how manly you are if you also strive for perfection you develop stress to get there.. Crossdressing helped.
I also made good friends around sport of all ages and had a surge in Women when I was around 18 over 12 months met a girl in Uni and dated for a bit but she smoked so dumped her, snogged a friend of Esmes (before we got together) and dated her for a bit but her mother I think told her she couldn’t date me as I was 2 years older so that fizzled out) and then some older woman who lied about her age to me (to be fair she looked a lot younger than she was) chatted me up and we snogged the night before she was going abroad.. step up a week away with friends in a Caravan and thats where me and Esme who was a friend of a friend met and that’s that for the last umpteen years.. Incidentally the older woman the night we returned back from our little holiday was in the same pub as me and Esme (now my GF as I’d asked her out and to be fair got to know her more in a week than the other girls I’d dabbled with over a longer period) and I had to quietly tell the older woman to go away lol.
So my experience with women before Esme was very little being so involved with my sport and shy.
With this for me came a stop to crossdressing for a few years.
We were also late losing our virginity 19 or 20 maybe but we couldn’t keep our hands off one another lol.
We moved in together at 22/24 got married when I was 25 I think so for the time between 19 and 24 I didn’t crossdress.
I do remember wondering what Lingerie etc Esme had and tried some on but nothing regular.
Then one day she asked to dress me as a woman and I finally agreed thinking had I put her knickers back wrong and she noticed and sussed I’d worn them? Was she calling me out as a crossdresser.. the answer was no but here I was letting her put makeup on me and dress me fully as a woman and it ignited a spark in me of wow I liked that lets do it again so I started dressing sometimes when I was home alone and also admitted to her I was a crossdresser… In her mind omg Gay, wants to be a woman etc etc but I’d only been dabbling in trying on lingerie until she put me in a dress and makeup and I looked ok as a woman that kick started it a bit for me.
I’ll wait for Katies part 3 to add my next steps and some reasons why I crssdressed more regular and moved from trying things on to makeup etc...